


A HALsteadMARK Christmas

by existential1rony



Category: Chicago PD (TV)
Genre: Christmas, Eventual Romance, F/M, Fluff and Angst, Unresolved Sexual Tension
Language: English
Status: Completed
Published: 2018-11-28
Updated: 2018-11-28
Packaged: 2019-09-01 14:47:30
Rating: Teen And Up Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 6,690
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16767247
Author URL: https://archiveofourown.org/users/existential1rony/pseuds/existential1rony
Summary: Jay and Hailey get sent on an undercover mission to a lake house a few days before Christmas. Will they make it back in time to see their families for the holidays? Will they even want to? An ode to Hallmark Christmas movies...





	A HALsteadMARK Christmas

It was December 21st, in the heart of the holidays, and Jay Halstead and Hailey Upton were en route to a stake-house in Lake Michigan. Their latest mission is to keep tabs on a rank-climbing Chicago mobster who has a vacation home on the lake. They’ll attempt to be deep undercover as a couple who are renting a house for a Christmas vacation. Neither was too thrilled when Voight picked them for this assignment, not because of anything it entailed, just the simple fact that it was so close to Christmas. He insisted they should be back with their families before the holiday, and it made the most sense they were the partners chosen if not. Their friendship & chemistry aside, neither are as close to their families, or a parent or guardian like some of the others in Intelligence. Still, who likes working and being away from loved ones around the holidays?

Jay was intent on making the best of it for himself and Hailey, because he knew it was affecting her harder than she let on. She doesn’t get to see her brothers often anymore, especially with this job, and they were all coming home to be with their mom this Christmas. Jay glanced at Hailey staring out the window as he drove, and racked his brain to think of something to lift her mood.

“We should be there shortly. Y’know, Antonio told me this house is a real sweet set-up. He said they boasted about a 65-inch 4k TV with a sports package. Blackhawks play their Christmas game in two days.”

Hailey turned her head to look at Jay and gave him a small smile. “That’s great! It’ll be real fun trying to pull you away from the couch.” She jokes.

“Hey! I am nothing, but professional. I can multitask and monitor the TV and the criminal at the same time!” This gets a laugh and a slight eye roll out of her and he’s happy for it.

The GPS talks and alerts them they’re two miles from their destination. They’re in an upscale section of the lake that’s isolated with only one entrance in and out. Sporadic mini-mansions are on their right, while the lake sits off to the left. Both Hailey & Jay’s eyes go wide with how nice it is staring out the windshield.

“Wow, maybe this assignment won’t be too shabby after all!” Hailey says. Jay grins; glad her spirits are boosted some. She’s the last person in the world he wants to see unhappy.

* * *

The two have finally arrived and have already unloaded Jay’s truck, including a bunch of groceries and a cooler filled with beer. Hailey had given him a questioning look when he had put all the beer in their shopping cart, to which Jay just replied with a grin & a shrug, “Might as well look the part of a true vacationer!” She couldn’t argue that and laughed.

Their house isn’t quite as big as the others, it’s actually a “guest house” off of one of the mansions, but it’s still awe-inspiring and in perfect sight of their target’s house. Once inside and unpacked, Jay of course made sure to get the beer in the fridge, they started setting up all their surveillance equipment. The mobster, John Reilly’s, house is a few hundred yards away to the left on a bend, allowing access to record the inside of the front of the house. Earlier in the week, Adam and Kevin had posed as routine fire inspectors and one of the maids let them inside. With that they were able to place a few bugs around the house for Jay and Hailey to tap into. Antonio’s CI had given them intel that Reilly was to spend the Christmas break with his family at the lake house. At the moment, there was just one car in the driveway and all seemed quiet.

“Now that everything is setup, let’s check out the rest of this place.” Jay says excitedly grabbing Hailey’s hand and pulling her along.

“Wow Jay, you’re like a kid on Christmas right now.”

“How can I not be? LOOK at this place!”

Hailey laughs. “No, I get it, but it’s not like we’re on a real vacation. We are gonna have to work at some point.”

“I mean, of course, yes. But I’m excited to enjoy this with you too.” He smiles at her and Hailey gives him a questioning look.

“Ok fine, if you’re excited, then I’m excited too.”

They explore the three bedroom house in shock and awe. The television is as described, hanging over a huge fireplace, with reclining sofas surrounding it, and a decorated tree next to the fire. The kitchen is just as huge, with sliding doors out to a big deck staring out at the lake. There’s a separate game room with darts, a pool table, and an assortment of board games, not to mention another TV. Each bedroom is also pretty big with queen size beds, and the master has its own bathroom with a hot tub.

“Rock, paper, scissors you for the master?” Hailey says eagerly, her smile beaming at how nice the place is.

“Nah, it’s ok, you take it. I’ve slept in army holes, I’m good anywhere. Plus, I’m enjoying seeing you this joyful.”

“Such the gentleman, Jay. Thanks for being so understanding with my bad mood this week, I know I’ve been a pain in the ass.”

“No apology needed, I understand. It’s going to be rough potentially not seeing our families for Christmas. But, I promise I’ll try to get you back to them before, even if I have to shoot Reilly dead to do it!” he jokes.

“Eh, it’s not so bad, I can think of worse company to be in. We’re basically getting paid double-time to hang out, which we do anyway, and in a much better location.”

“Aww, now there’s the Christmas spirit, Hailey, cha-ching!” Jay laughs and puts his arm around her, doing a fake choke hold as he walks her back to the kitchen where all their equipment is.

The rest of the night went by pretty uneventfully. There wasn’t much movement in Reilly’s house, so Jay & Hailey decided to call it an early night since they arrived pretty late anyway, and get an early start in the morning

Hailey wakes to the smell of coffee and bacon. She makes a small groan when she grabs her phone to check the time and see it’s only a little after 7. She stretches out her arms and reluctantly yanks off the covers to get up.

When she enters the kitchen she stops dead in her tracks as she sees Jay standing over the stove cooking eggs, shirtless in just his boxer shorts. Her jaw drops and it takes her seconds to formulate words and to stop staring at him longingly. She quickly tries to shake herself out of it. Now is not the time for the… feelings… she’s been having for him to resurrect.

“Man, when you say ‘early start,’ you really mean early!”

Jay turns to see Hailey standing in the doorway in her long shirt and bootie-shorts pajamas. He gulps to cover his reaction before speaking.

“Sorry, force of habit waking early. I can never sleep in alone. I hope I didn’t wake you, but I did make breakfast.”

“No, and it smells delicious, thank you. And the coffee is a God-send.” She says as she walks past him to pour herself a cup and grab a piece of bacon off the plate. She closes her eyes and relishes the taste of the fried pork. “Mmm. So why can’t you sleep in at all? Not like we’re going to the gym today.”

“I don’t know, guess it was just drilled in me so much in the army days; my eyes just kind of pop open by 6 every day. If it’s more than just me in the bed, I’ll try to force myself back to sleep, but it’s still hard.”

Hailey does her best to not think about someone else in Jay’s bed and changes the subject.

“So, did you hear Reilly or anyone in the house yet?”

“Not yet. I saw a few maids pull up a little while ago and let themselves in, but nothing out of the ordinary. I don’t know when his family is going to arrive. I figured once we ate and got dressed, we can try to explore outside a little, see if we notice anything.”

“Sure, that sounds good. But first, I’m going to need at least two cups of coffee.” She says as she grabs another full cup and heads into the living room. Jay laughs and watches her back as she walks away, shaking his head.

* * *

A little after 9 they’ve finally made their way bundled outside. They slowly make their way up a path between the mansions. No real plan in mind, they hope to see if they can see anything in their snooping.

As they turn around one little bend, they stumble across an older woman with groceries going into the mansion behind them. She stops unloading her car when she sees them and waves.

Jay and Hailey give each other one of their side looks and slowly walk over.

“You must be the Berkfield’s renters. I’m Mary, the caretaker, so nice to meet you. This is such a magical time to get away by the lake.”

They realize that she must work at the mansion whose “guest house” they’re staying at and play along with their covers.

Jay extends his hand to shake. “Hi Mary, nice to meet you. I’m Tom and this is my fiancée Jenny.” Hailey reaches out to shake hands.

“Oh, what a lovely young couple. What brings you out here? Normally Mr. Berkfield only rents the carriage house to his clients.”

Jay and Hailey glance at each other, and Hailey takes it. “Oh, well we really made a case with the realtor. My parents used to take us kids up to Lake Michigan when I was a young, all the way from Cedar Rapids, and ever since they passed away, the holidays haven’t been the same. Tom thought it’d be a great idea for us to get away, and here we are.” Hailey raises her arms in a shrug and grins at the older woman, really trying to sell it.

“That’s just marvelous. I’m terribly sorry about your parents though. My husband passed away a few years ago, so I know how hard the holidays can be. And don’t you know he was from Iowa too! What a small world.”

“Wow, that’s really funny.”

“I hope you don’t mind me asking, how did you two lovebirds get together?”

Hailey shoots Jay a look, silently letting him know this one is his turn.

“It’s really not all that romantic. Jenny was partnered up with me at our advertising firm shortly after I returned from overseas and I was insufferable to her. She was patient and forced me into realizing I probably needed therapy to help, and I finally caved. After months of sessions, it registered that it was the best thing anyone had ever done for me, especially being so understanding, and I fell for her. Shortly after, I asked her out.” He notices Hailey eyeing him suspiciously and quickly adds, “Nothing special.”

“Nothing special? Why I gather you can say she saved you, isn’t that right? If that’s not romantic, I don’t know what is.” Hailey looks down.

Jay fidgets a second, “Yea, I guess so…” He quickly looks to change the subject. “Anyway, will you be here through Christmas? Do all the neighbors normally hang around?”

“Oh no dear, I’ll be going home to my kids later today. The Berkfield’s normally stay in the Alps until New Years; and the Reilly’s over there, I can’t really keep up with them. There’s always people coming and going in that house. You know,” she starts to whisper and wiggles her finger for them to come closer, “I hear that Mr. Reilly is a shady character. All just rumors, but I think they’re true. I never did get a good vibe from him, but you didn’t hear it from me!”

“Well, we’ll be sure to avoid that house then.” Hailey says.

Jay seconds it. “Yes, we will. Can I help you get those groceries in? We should be on our way soon.”

“I’m fine dear, thank you. You two lovebirds go enjoy! So nice meeting you. And don’t forget, there’s a storm coming through tomorrow, be careful, it definitely comes down harder out here.”

“Thank you, we will. Very nice meeting you!” Hailey and Jay say as they walk away. As they start walking back to their house, Hailey debates questioning Jay about his story, but chickens out. She resigns that he was just playing his cover.

* * *

It’s 2pm when they finally hear talking from the bugs in the Reilly house. Jay and Hailey jump off the couch from their heated debate on whether to watch the “SVU” marathon or “It’s a Wonderful Life,” running to the kitchen to their listening devices.

They make out three male voices. Jay grabs his binoculars to peer through the suspect’s kitchen window. He recognizes Reilly as one of the guys, and what looks like two of his counterparts.

“Reilly is definitely in there, and I think the other two are Little Tony and McGregor.”

Hailey grabs the camera and starts snapping pictures with the long lens.

“I told you guys, this week is my family time. We’re not supposed to be dealing this yet. ..”

“…Yes, but the shipment is arriving sooner than we thought. We have to prepare the docks for the 27th now…”

“…I don’t like this, let’s go talk in the basement…”

The audio cuts off with footsteps walking away.

“Shit, you think they know we’re here?” Hailey asks.

“Nah, there’s no way they can suspect, probably just being cautious. You know how mobsters are. We’ll catch them when they come back up. Now, back to our discussion… how can you possibly not want to watch ‘It’s a Wonderful Life’ so close to Christmas?”

“Y’know Jay, normally it’s women who are obsessed with that movie. I find your taste more suspicious.”

“EXACTLY my point, last I checked, you are in fact a woman!” Hailey raises her brow at him. 

“Oh, you know what I mean. I’m not checking your woman parts out. Not that they’re not great parts, ugh, I mean, I’m just gonna shut up.”

Hailey laughs, feeling sorry for her tongue-tied partner. “Yes, I get it. I don’t know, I was just never fond of that movie, always struck me as a little boring. I was much more of ‘A Christmas Carol’ kind of girl. My brothers and I always watched that when we were kids because we thought Scrooge reminded us of dad. It gave us hope that if Ebenezer Scrooge could change his disposition, then maybe he could too…”

Jays listens intently as Hailey slightly drifts off into her saddened memory.

“Any who, every Christmas my brothers would make me cinnamon buns, flatten them like a pancake on a skillet into a weird shape, and drape the icing around it to make it look like The Ghost of Christmas Past. Corny, I know.”

Jay chuckles quietly. “That’s not corny, your brothers sound great.”

“Yea, they really are. I think you’d get along with them… most of the time.”

“I can’t wait to meet them one day. That story though, it does explain a lot about you and your cooking skills…” Jay jokes.

Hailey chucks a pillow from the couch at his head.

“You better watch it Jay, or I’m going to tell everyone you’re a huge James Stewart groupie!”

He raises his hands in surrender.

* * *

It’s nearing 7:30pm when their surveillance audio pops up again. They had just finished dinner. Jay cooked again, and Hailey had thought about being offended, until she realized she was being served work-free meals. She took it as a win and made the drinks, they had brought a bottle of whiskey as well.

This time the only voice on the recording is Reilly’s. Once they run over and grab the binoculars, they realize he’s on the phone.

“I know honey… yes I know I promised… but business comes first. We’ll take the kids to the Alton house on Christmas Day instead. I’m leaving tonight, I already sent the maids home, and I’ll be back there for Christmas Eve. We’ll spend the kids Spring Break here… Yes… Look, I’m sorry, but I got to go. I have a deadline. I’ll call you when I get there…”

“Shit, it sounds like he’s leaving for good, right?” Jay asks.

“Yea, what do we do now? Call Voight? He’s gonna be pissed!”

“There’s not much we can do, I’ll call him.” Jay grabs his cell phone out of his pocket.

“Hey boss… everything’s good, but it sounds like Reilly is leaving the house… No the intel was right, but he told his family he has to cancel. They have some deal going down on the docks on the 27th… Yea, ok. Sounds good, will do!” he hangs up the call.

Hailey looks at him expectantly, with her ‘waiting face’ on.

“He wasn’t as disappointed as I thought. He told us to feel free to return home to be with our families if we want and that we’d try to tail Reilly again next week.”

“Oh wow, ok, awesome. Sucks that we didn’t get much, but at least we won’t be stuck here for Christmas. Although, I must say, I really am enjoying these digs. Guess we’re leaving first thing?”

“Yea, if that’s alright with you. It’s a long drive and already getting late. The snow’s not supposed to start until the afternoon, so we can leave early in the morning. We’ll still be home the night before Christmas Eve.”

“That’s perfect. Plus, I just made us drinks, and we haven’t gotten around to me besting you at pool yet.”

“Hailey, Hailey, Hailey, you’ll never best me at pool. ‘Eight-ball’ is my middle name!”

Hailey scrunches her face at him. “Uh Jay, two things… 1) as a cop, you may not want your nickname to also be a recreational drug reference. And 2) you wish!”

“Ok, fair point… and you’re on!” . . .

After three rounds of pool (Hailey won two of them) and four whiskey-gingers later, Hailey and Jay decide it’s time for a good night’s sleep. It’s mostly Hailey who decides. With the alcohol and ambiance of the lake house, things are starting to get flirty between them and she has to stop it. If not for her sanity, then for her heart.

“I still can’t believe you beat me twice. This table must be slanted or something!”

Hailey gives Jay a look. “And what exactly would that do? We’re both shooting from any given angle.”

“I don’t know, you’re shorter?” Jay states, more as a question. “C’mon, let’s just play one more game. How often do we get to have some down time?” He pokes her in her hip with his cue stick and gets her in a rather ticklish spot.

She bats the stick away while giggling like a little girl, but quickly pulls it together. “No, c’mon, seriously Jay. We said this was it since we have to wake up early, and you already know I’m not a morning person!”

“Okayyyy boss” Jay pouts as he puts his stick on the table.

They walk into the hallway together where the bedrooms are. There’s an awkward pause as they each stand outside their rooms. Jay wants to give Hailey a hug, but decides against it. Instead he puts his hand up for a high-five. Hailey looks at him weird, but slaps his hand anyway as she says “Good Night,” then walks into her room and closes the door disappointed.

“Did he just high-five me like a 10 year old kid!?” she wonders out loud.

Jay bangs his head on his door exasperated. “I’m an idiot!”

* * *

At 6:03am Jay’s eyes pop open like clockwork. He stretches and gets out of bed. He walks over to the window and pulls back his drapes.

“OH SHIT!” His eyes bug out of his head as he stares at a blanket of snow on the ground with the flakes still rapidly coming down.

The first thing he thinks of is Hailey. There’s no way they’re making it out of here today. She was so excited when she called her brothers last night to tell them she would indeed be home by Christmas Eve. The chances of that now have dwindled immensely. His heart breaks knowing she’s going to be disappointed when he wakes her.

He slowly creeps over to her room and softly opens the door. He takes a second to watch her sleep. She’s hugging the covers to her and looks so peaceful and beautiful. He’s in awe and lets out a deep sigh.

He hesitantly walks closer to her bed and gently calls her name. “Hailey.” She stirs a little, but doesn’t wake.

He gently touches her arm and tries again, “Hailey, it’s me, wake up.”

Her eyes start squinting as she opens them and she lets out a small groan. “Ugh, is it time to leave already? It’s so early!”

“Yea, well, about that…”

She hears the somberness in his tone and instantly pops up. “What, what’s wrong?”

“Um, well, it seems the snow came a little earlier than we thought…”

“What? NOOO!” She shoots up from bed and runs over to the window. “Crap! What are we supposed to do now?”

He looks at her sympathetically. “Given the fact that this looks like a blizzard, and these rich back roads aren’t on the State’s important list, I doubt they’ll be plowing any time soon. Looks like we’ll be stuck here for a while, at least until tomorrow.”

“But, tomorrow is Christmas Eve… I promised my family I’d be back.”

“I know, I’m sorry. If I had known this would happen, I swear I would have made the drive last night.”

“No, it’s not your fault, neither of us could have known. Apparently, neither did the weathermen. Ugh, I just can’t believe we’re trapped here, some Christmas this will be!” she shakes her head disappointed.

Jay purses his lips and looks down. “Yea, well, I’m gonna go make some coffee.”

Hailey realizes how bitchy she sounds and quickly tries to apologize. “Not that spending it with you is bad, Jay, just…”

“Yea, I know, I get it. I’ll be in the kitchen. Take your time, looks like we’ll have a lot of it.” He walks out of her room solemnly.

Hailey takes the opportunity to flop back down on the bed and slam her head in the pillow. “AUGH!” she screams into it. She didn’t mean to react the way she did, this was just not what she was expecting to wake up to. Plus, if she’s being truly honest with herself, which she tries to avoid at all costs, next to her family Jay is probably the next person she’d want to spend the holidays with. It’s going to be a long couple of days for her emotions.

* * *

Jay is sitting on the couch watching NFL Network when Hailey comes out of her room finally. He glances at her quickly from the corner of his eye. All he says is, “I left the coffee on for you.”

“Thanks, I appreciate it.” She walks over to the counter and starts pouring herself a cup. A minute or two goes by and Jay speaks again.

“I just toasted one of the Eggo waffles and ate that, but I can make you something if you want?”

“No, I’m good, thanks. I’ll probably just have some cereal….”

“Hailey…”

“Jay…”

They both speak at the same time and laugh. “You go,” Jay says.

“I’m sorry about before. I really do enjoy spending time with you, it just wasn’t the news I was expecting.”

“I know. I promise we’ll have fun while we’re here, and I’ll get you back to your family the first second I can.”

She smiles at him and walks over to sit on the adjoining couch. “I don’t doubt it.”

“Hey, you think Voight will still override this as overtime for us?” she asks him.

Jay cracks up, “Yea, I doubt that…”

She laughs too, “Eh, it was worth a shot… I know what we should do first.”

“What’s that?”

“Watch ‘It’s a Wonderful Life’”

“You just said yesterday how much you dislike it.”

“I do, but maybe watching it with you I’ll see it differently.”

Jay smiles, “You’re just sucking up for the coffee and everything at this point, but I’ll take it.” He switches the TV to the video service on the remote and finds the movie.

The next couple of hours they quietly enjoy each other’s company and watch the movie.

* * *

It’s a little later in the afternoon when the snow finally stops. Jay and Hailey have already watched the movie, played a few rounds of darts, and ate lunch. Once they see the snow has stopped, Hailey thinks it’s a great idea to go outside and make a snowman. Jay reluctantly agrees, solely because he likes seeing her happy.

They have gathered the first two big snow mounds to make the body when they decide to take a quick break. The sun had come out a little bit and it’s starting its early Winter setting. They find a log to sit on that was covered by being under the deck and admire the view over the lake.

“Y’know, this would be a great place to come vacation at in the Summer. I only came here once when I was younger.” Hailey says.

“Yea it would, we should get a group of us together. My parents didn’t do many family vacations when Will and I were kids. We went to the Jersey shore a couple of times, but that was about it. I’d love to do some water sports on the lake.”

“Why, so I can beat you in them too?” she pushes Jay’s arm laughing.

“You’re getting way too cocky there, Upton. Better watch out!”

“Nothing you can do about it, Halstead.”

He raises his brow at her. “Oh, really?” She smirks back, not realizing that he’s grabbing a handful of snow with his hidden hand.

Once she turns her head straight again, Jay takes the opportunity to smash the snow he gathered on top of her hat and forehead. She jumps up like a shotgun from the log.

“OH NO YOU DIDN’T!”

Jay cracks up hysterically. He throws his hands up as she starts throwing snow at him.

“Hey, c’mon now, I’m gonna get all wet. Truce?” he asks.

Hailey drops down her hands to her sides.

“You’re right, we’re adults, we should behave like them.” She says, but once Jay breathes a sigh of relief she throws the last snow ball she has and it smacks him right on his upper chest. Hailey jumps around exuberantly laughing.

Jay’s eyes go wide. “Oh, that’s it. You’ve done it now, Upton!” He hops up, wraps his arms around her waist, and tackles her to the ground. They roll around laughing and Jay smashes more snow into her face.

“Ok, ok, mercy! You win, I fold.” Hailey finally says after a couple minutes not gaining back the upper hand. Jay beams triumphantly, stands, and reaches his hands out to help her to her feet.

He can’t help but notice how the little bit of snow left around her face is illuminated by the Christmas lights and to him she looks like an angel.

Hailey thinks he’s staring at the last of the setting sun over the lake. “It really is beautiful, isn’t it?”

“Yea, it is…” Jay says gruffly. It’s only then that Hailey realizes he’s looking at her longingly. Her heart starts beating rapidly and she thinks she freezes. Before she even realizes it, they’re both leaning in at the same time and kissing.

A couple of seconds, or maybe its minutes go by, when a deer runs by in the background, startling them apart. The moment is broken and they both stare at each other questioningly.

Hailey is the first to break the silence as she slowly starts backing away from him. “Uh, I should get inside and shower. My clothes are pretty soaked and I don’t want to get sick…” she starts walking quickly to the deck stairs.

“Yea, no, of course. I’ll be in in a sec.” Jay says, still in shock. He stares out at the frozen lake, thinking he should be mad at himself for losing control and kissing his partner; especially since he lasted so long without acting on his feelings. But, all he feels is peace.

* * *

The next couple of hours go by a little awkwardly for them. They both help with making dinner, just simple pasta, but don’t speak all that much. They especially don’t dare to talk about what happened outside. Luckily, the Blackhawks game is on tonight, so it gives them both an excuse to focus on that.

Jay keeps glancing at Hailey, sitting a couple of feet away from him, but he doesn’t really know what to say. She’s obviously deeper in thought then him, and probably regrets it more. Whereas, he can’t help but feel it was right.

Hailey notices every time Jay looks at her, and it’s starting to make her antsy. She’s so torn inside. Part of her wants to ask him if the kiss meant anything, and the rational side of her knows the smartest thing is to forget it. Finally, she caves and decides to ask him something that’s been on her mind the past few days.

“Jay…”

“Yea?” He puts down his beer, realizing the face she’s giving him is a serious one.

“That cover story you told Mary about us the other day, that hit a little too close for comfort, no?”

“What do you mean?”

“Well, I actually am your partner, and I kind of did force you into therapy…”

“You are and you did. And I’m forever grateful to you for it; I told you it had really helped me!”

“I know it did, and I’m glad… but, what about the other stuff you said? You said you fell for her…” Hailey drifts off hesitantly.

Jay stares into the fire for a bit before answering, contemplating how to play this. “What do you want that answer to be, Hailey?”

She looks down and picks at her sweater sleeve nervously. When she looks back up, she looks directly at him sadly. “I don’t know what you mean…”

“Do you want my answer to be, ‘yes, I have fallen for you’? Or do you want it to be all about some BS cover story that I made up? Because this moment kind of comes down to you Hailey and what you want…”

“Jay…” Hailey warns, tilting her head at him, not really knowing what else to say.

“Oh, fuck it!” he says right before he lunges forward and kisses her. When he realizes she’s not pulling away and punching him, he deepens the kiss. A minute or two passes, and then Hailey is wrapping her arms around his neck. Shortly after, Jay is on top of her on the couch, and shirts getting pulled off soon follow. Jay grins at her happily as they break away for a second, but Hailey grabs his head and starts kissing him again. She doesn’t want to think about this moment, she just wants to feel for once. She can think about the repercussions later…

* * *

It’s a little after midnight when Hailey wakes to realize she’s on the living room floor in front of the fire, wrapped in a blanket, with Jay’s arms around her. Right away, the fear of her emotions creeps in. She’s already contemplating in her head all the ways she can get out of this without hurting him. It’s not that she doesn’t want this, because she so does, it’s more that she’s scared. It’s much easier to hold people at arm’s length, than it is to let the feelings in and risk hurting one of them, or worse, losing him… And she can’t think of her life without Jay in it.

She feels him start to stir, so she slowly begins to pull away, covering herself with the blanket.

“Where are you going?” she hears him ask groggily into his arm.

“Um, I think I’m going to head to actual bed, it’s pretty late now.”

Jay’s sitting up now as she stands, and Hailey has to force herself to be strong and look away, because he’s naked… very, very naked…

“Well, wait just a second, I’ll come with you…”

“No, I think it’s best if we go to our separate rooms. This was fun and all, but…”

He stares up at her and she instantly knows he’s angry. She can’t really blame him, she’s a weak jerk.

“Hailey, seriously!? We’re not going to do this! You’re not going to pretend this just didn’t happen!”

“I’m not pretending. It was great, I mean, it was REALLY great… I just think it’s best if we don’t mess up our partnership. We got this out of our system, and we can move on. I mean, it was only a matter of time anyway, right?”

“Dammit Hailey! Can’t you for once admit your feelings? I’m not saying I’m much better in that department, but fuck; I’m done running from this! I know you feel the same way. I know it. I KNOW YOU! Why are you still fighting this?”

Tears well up in Hailey’s eyes, and she almost caves… almost… “I can’t be who you want me to be. Look Jay, I’m going to go to bed. You’ll see in the morning that this is what’s best.” She walks towards her bedroom with the blanket wrapped around her, leaving Jay hurt and shocked on the living room floor.

“Yea, sure Hailey, Merry Christmas!” he yells out.

She closes the bedroom door and finally lets the tears take over. 

It’s around 5:30 in the morning when Hailey wakes up. Well, “wake up” is a strong term; she didn’t sleep all that well. She spent all night tossing and turning thinking about Jay. She knows he’s right, and she knows she has feelings for him, has always had feelings for him… but where they’re at has worked so well for them. It’d be foolish to jeopardize that, right? Especially with how dangerous their jobs are.

She throws the covers off and gets up, realizing she has to talk to him some more and better explain her side. He deserves that at least. She walks over to his room and opens the door, only to find that he’s not there. Thinking he probably stayed in the living room, she heads that way. When she sees he’s not there either, she starts getting a little worried.

She rushes over to the window to see his truck is still outside and the road still doesn’t look plowed. “What the Hell?” she thinks out loud.

Hailey runs back into her bedroom and grabs her phone. She pulls up Jay’s number instantly and texts him asking where he is.

He gets back relatively quickly… “Sorry, didn’t think you’d be up this early. Had to run an errand, everything is ok, don’t worry. Be back later.”

Hailey feels a little better, but still wonders what the heck he can be doing at this time, especially without a car. She sighs, realizing their conversation is going to have to be postponed, and tries to fall back asleep. She doesn’t think it’d be possible, but a wave of tiredness hits her hard and she’s fast asleep.

It’s around 8:30 when she wakes back up. She shoots out of bed, instantly wondering if Jay is back, in fear in case he’s not.

She walks out to the living room and breathes a sigh of relief as she sees Jay’s in the kitchen doing something by the stove.

“Thank God, where the Hell did you go?”

“Well, good morning to you too, Hailey!” Jay responds smirking.

“Seriously, you freaked me out. Who vanishes from a cop? Especially when a known mobster lives across the way!”

“Um, another cop who just had to run an errand…” He says so nonchalantly that it kind of irks her.

She’s about to lay into him some more when she smells a whiff of cinnamon and her stomach growls; curiosity peaked, she walks over towards the stove to see what he’s making.

Her jaw drops when she realizes what it is and she feels all her emotions bubble to the surface… cinnamon buns… Cinnamon buns that Jay is flattening into pancake shapes.

Jay senses her staring and finally fills in the blanks for her. “I know how upset you were that you couldn’t get back to your family sooner; and since you said your brothers used to make you these as tradition, I just wanted to bring a piece of that to you…”

Tears well up in her eyes as she realizes why he must have left, and how sweet of a gesture it was. “But Jay, we didn’t have these in our groceries, how did you pull this off?”

“I know, I went to the store this morning to purposely get them.”

“But, how? The roads aren’t even plowed yet?”

“I walked… the closest one was only 2.5 miles away.”

Hailey stares at him in shock, and adoration. “You WALKED 5 MILES IN THE SNOW just to buy a package of cinnamon buns!?”

Jay puts the spatula down and stares at her. “Hailey, I’d walk a 1,000 miles in the snow to make you smile…”

Tears stream down her face as she grins at him.

“Look, I know last night you said…”

Jay’s words get cut off as Hailey grabs him by his neck and kisses him.

When they break apart he leans his forehead against hers.

“What happened to you not wanting to change the dynamic of our partnership?” he asks while smiling.

“Shutup, Halstead. I’m an idiot!” that’s the last thing she says before she starts kissing him again. They don’t get around to eating the cinnamon buns until hours later…

* * *

Jay comes back inside from cleaning the snow off his truck to see that Hailey is still wearing just his oversized Blackhawks jersey. His heart does flips as he watches her on the couch scroll through the channels. He can’t remember the last time he’s been this happy, if ever. He brushes the snow off his jacket and hangs it up. Then he walks over to Hailey and plops down next to her. Her smile beams up at him when he sits.

“They’ve finally plowed the road. So if we leave soon we can get back to Chicago well before Christmas morning!” he tells her, assuming she’ll be ecstatic.

Instead, she uses the opportunity to straddle his lap. He looks up at her questioningly, but chuckling.

“Eh, we could stay here until the morning. You wake up early anyway. This place has kind of grown on me…”

“Is that so? So you want to shack up with me here another night when we don’t have to? That’s naughty, Upton! What would your brothers say?”

“Well, it’s probably better you don’t tell them when you meet them tomorrow.”

“Does that mean you’re inviting me to Christmas dinner? That’s a pretty big step…”

She grins at him. “Shutup!” she says right before she starts kissing him. It’s starting to become Jay’s favorite word… He grabs her hips under the jersey and swiftly carries her into the bedroom. His final coherent thought before he loses all control is that this undercover mission turned out much better than they expected… even if they accomplished almost nothing work-wise, he’ll take it as a win. James Stewart would approve!

**Author's Note:**

> [A/N: I'm a huge fan of the cheesy Hallmark & Lifetime Christmas movies this time of year, and I thought who better than Upstead to incorporate into a story like them!? I also hate how most shows go on hiatus well before the holidays now, the holiday episodes used to be my favorite. Anyway, sorry if it's a little long, I may have gotten carried away. Thanks again for reading (& all the kind reviews) my stories. I'm so glad you've enjoyed them. Happy Holidays to all of you! 3]


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